Glycolic acid esters of 2-phenylquinolin-4-carboxylic acid.



and rheumatism etc.

UNITED srrrrns PATENT orrrcn.

GLEMENS'ZClI-LNEB; 0F

FABRIK 'AU'E ACTIEN CHARLOTTENBURG, GEBMANY, ASSIGNOR T0 CHEMISCH E'(VORM. E. SGHEBING), OF BERLIN, GERMANY.

GLYGOLIG non) nsrnns or a-r'nnnvnoumonm-a-cnrnaoxvmo ACID.

o Drawing.

Specification of Letters Patent.

' Patented Feb. 10, 1914.

7 To allivhom it may concern:

V 1 Queen.

in which R is an alcoholic radical. The new compounds are insoluble inWater, soluble 1n the usual organic solvents, are nearly tasteless, andare useful as remed es 111 gout the production of the new The processfor compounds consists 1n causing a halogen-' acetic ester to react upona salt of the 2- phenylquinolinl-carboxylic acid.

In order to illustrate my invention, the following examples are given,the parts be ing by weight:

1. Molecular quantities of the sodium salt of phenylquinolin carboxylicacid and the ethyl ester of c'hloroa'cetic acid are dissolved in alcoholand heated under pressure for from four to five hours to about 120 centirade.- The filtrate from the precipitated sodium chlorid is evaporatedand fractionated in cacao the alcoholic and chloroacetio ester residuespassing over first. Above 250 centigrade at a pressure of 15millimeters.

the 2 phenylquinolini-carboxylic acid-glycolic acid ethylester passesover as'a clear slightly yellow oil having a pleasant aromatic odor. Theester is soluble in alcohol, ether. chloroform, acetone and in olive o land can be employed as a liniment either directly or when suitablydiluted. The 011 can removed by Application filed August 13, 1913.Serial No. 784,621.

be brought to a crystalline state by the addition of a few crystals andthe crystals obtained melt at 60 centigrade which can again be renderedfluid by heating.

2. 20.4 parts of the sodium salt of phenylquinolin carboxylic acid inalcoholic solution are heated to 125-135 centigrade together with 17 .4parts of chloroacetic acid menthylester for four hours in a closed tube.After v cooling the precipitated sodium chlorid is filtration and fromthe filtrate the phenylquinolin-carboxylic acid-glycolicacid-menthylester is after distillation of the alcohol obtained as athick oil soluble in the usualcorganic solvents. f

Other esters are obtained in a similar manner.

I claim as my invention: 1. As new products the glycolic acid esters of2-phenylquinolin-4=-carboxylic acid of the formula COO.CHz.COOR

in which R is an alcoholic radical, which products are insoluble inwater, soluble inthe usual organic solvents, are nearly tasteless andare useful as remedies, substantially as described.

2. The herein described glycolic acid ethylester ofQ-phenvl'quinolin--carboxylic acid of the formula (fOOllHz-COOCzHs beinginsoluble water, soluble in alcohol, I

ether, chloroform, acetone and in olive oil, substantially as descrlbed.3. The herein described process of produciiig glycolic acid esters of2-phenyl quinolin- L-carboxylic acid, which consists in my hand in thepresence of two subscribing causing a halogenacetic ester to react uponwitnesses. a salt of the 2-phenylquin0lin-4-carboxylic CLEMENS ZOLLNER.acid, and isolating the product of reaction, Witnesses: 5 substantiallyas described. I I'IENRY HAsPER,

In testimony whereof I have hereunto set HARRY L. lVILsoN.

